反应详情

To a solution of the product from Example 1C (865 mg, 3.19 mmol) in anhydrous tetrahydrofuran (30 mL) was slowly added a tetrahydrofuran (10 mL) solution of (2-carboxyethyl)triphenylphosphonium tribromide (1.85 g, 3.19 mmol) at 0° C. The mixture was then stirred at ambient temperature for 2 hours. The mixture was partitioned between ethyl acetate and water. The layers were separated, and the aqueous layer was washed with additional ethyl acetate. The organic fractions were combined, washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel eluting with 10% ethyl acetate/hexanes to provide the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 2.31 (s, 3H), 2.37-2.27 (m, 2H), 3.60 (t, J=6.4 Hz, 2H), 4.11 (t, J=5.8 Hz, 2H), 5.42 (s, 1H), 6.90 (d, J=8.8 Hz, 2H), 7.36 (d, J=8.8 Hz, 2H); MS (DCI/NH3) m/z 366 (M+NH4)+.

1. customThe mixture was partitioned between ethyl acetate and water
2. customThe layers were separated
3. washthe aqueous layer was washed with additional ethyl acetate
4. washwashed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was chromatographed on silica gel eluting with 10% ethyl acetate/hexanes